Details
Stereochemistry | ACHIRAL |
Molecular Formula | C17H19N2O5S.Na |
Molecular Weight | 386.3997 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCCNc1cc(cc(c1Oc2ccccc2)S(=O)(=O)N)C(=O)[O-].[Na+]
InChI
InChIKey=QDFGOJHAQZEYQL-UHFFFAOYSA-M
InChI=1S/C17H20N2O5S.Na/c1-2-3-9-19-14-10-12(17(20)21)11-15(25(18,22)23)16(14)24-13-7-5-4-6-8-13;/h4-8,10-11,19H,2-3,9H2,1H3,(H,20,21)(H2,18,22,23);/q;+1/p-1
Molecular Formula | Na |
Molecular Weight | 22.9898 |
Charge | 1 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | C17H19N2O5S |
Molecular Weight | 363.4099 |
Charge | -1 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionCurator's Comment:: description was created based on several sources, including:
http://www.rxlist.com/bumex-drug/side-effects-interactions.htm
https://www.drugs.com/cdi/bumetanide.html
http://www.wikidoc.org/index.php/Bumetanide_(oral)
Curator's Comment:: description was created based on several sources, including:
http://www.rxlist.com/bumex-drug/side-effects-interactions.htm
https://www.drugs.com/cdi/bumetanide.html
http://www.wikidoc.org/index.php/Bumetanide_(oral)
Bumetanide is indicated for the treatment of edema associated with congestive heart failure, hepatic and renal disease, including the nephrotic syndrome. It blocks the reabsorption of sodium and fluid from the kidney's tubules. The most frequent clinical adverse reactions considered probably or possibly related to bumetanide are muscle cramps (seen in 1.1% of treated patients), dizziness (1.1%), hypotension (0.8%), headache (0.6%), nausea (0.6%) and encephalopathy (in patients with preexisting liver disease) (0.6%). One or more of these adverse reactions have been reported in approximately 4.1% of patients treated with Bumex (bumetanide). Lithium should generally not be given with diuretics (such as Bumex (bumetanide)) because they reduce its renal clearance and add a high risk of lithium toxicity. Bumex (bumetanide) may potentiate the effect of various antihypertensive drugs, necessitating a reduction in the dosage of these drugs.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: P55011 Gene ID: 6558.0 Gene Symbol: SLC12A2 Target Organism: Homo sapiens (Human) |
3.0 µM [IC50] | ||
Target ID: Q9UP95|||O60632 Gene ID: 6560.0 Gene Symbol: SLC12A4 Target Organism: Homo sapiens (Human) |
60.0 µM [IC50] | ||
Target ID: Q9H2X9 Gene ID: 57468.0 Gene Symbol: SLC12A5 Target Organism: Homo sapiens (Human) |
55.0 µM [IC50] | ||
Target ID: Q13621 Gene ID: 6557.0 Gene Symbol: SLC12A1 Target Organism: Homo sapiens (Human) |
4.0 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | BUMEX Approved UseBumetanide Injection is indicated for the treatment of edema associated with congestive heart failure, hepatic and renal disease, including the nephrotic syndrome. Almost equal diuretic response occurs after oral and parenteral administration of bumetanide. Therefore, if impaired gastrointestinal absorption is suspected or oral administration is not practical, bumetanide should be given by the intramuscular or intravenous route. Successful treatment with bumetanide following instances of allergic reactions to furosemide suggests a lack of cross-sensitivity. Launch Date4.1523839E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
42 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/8312869 |
2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered: |
BUMETANIDE plasma | Homo sapiens population: UNKNOWN age: ADULT sex: FEMALE / MALE food status: FASTED |
|
111.38 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/22475517 |
2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered: |
BUMETANIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
167.34 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/8312869 |
2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered: |
BUMETANIDE plasma | Homo sapiens population: UNKNOWN age: ADULT sex: FEMALE / MALE food status: FASTED |
|
258 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/22475517 |
2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered: |
BUMETANIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1.88 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/22475517 |
2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered: |
BUMETANIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
5% EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/22475517 |
2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered: |
BUMETANIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
3% |
BUMETANIDE serum | Homo sapiens population: HEALTHY age: NEWBORN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
2 mg 2 times / day multiple, oral Recommended Dose: 2 mg, 2 times / day Route: oral Route: multiple Dose: 2 mg, 2 times / day Sources: Page: p.4 |
unhealthy, 14–18 n = 21 Health Status: unhealthy Condition: Autism spectrum disorders Age Group: 14–18 Sex: M+F Population Size: 21 Sources: Page: p.4 |
Disc. AE: Hypokalemia, Anorexia... AEs leading to discontinuation/dose reduction: Hypokalemia (moderate, 14.3%) Sources: Page: p.4Anorexia (moderate) Fatigue (moderate) Polyuria (moderate, 4.8%) |
10 mg 1 times / day multiple, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: Page: p.597 |
unhealthy, 22-72 n = 18 Health Status: unhealthy Condition: Renal edema Age Group: 22-72 Sex: M+F Population Size: 18 Sources: Page: p.597 |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Hypokalemia | moderate, 14.3% Disc. AE |
2 mg 2 times / day multiple, oral Recommended Dose: 2 mg, 2 times / day Route: oral Route: multiple Dose: 2 mg, 2 times / day Sources: Page: p.4 |
unhealthy, 14–18 n = 21 Health Status: unhealthy Condition: Autism spectrum disorders Age Group: 14–18 Sex: M+F Population Size: 21 Sources: Page: p.4 |
Polyuria | moderate, 4.8% Disc. AE |
2 mg 2 times / day multiple, oral Recommended Dose: 2 mg, 2 times / day Route: oral Route: multiple Dose: 2 mg, 2 times / day Sources: Page: p.4 |
unhealthy, 14–18 n = 21 Health Status: unhealthy Condition: Autism spectrum disorders Age Group: 14–18 Sex: M+F Population Size: 21 Sources: Page: p.4 |
Anorexia | moderate Disc. AE |
2 mg 2 times / day multiple, oral Recommended Dose: 2 mg, 2 times / day Route: oral Route: multiple Dose: 2 mg, 2 times / day Sources: Page: p.4 |
unhealthy, 14–18 n = 21 Health Status: unhealthy Condition: Autism spectrum disorders Age Group: 14–18 Sex: M+F Population Size: 21 Sources: Page: p.4 |
Fatigue | moderate Disc. AE |
2 mg 2 times / day multiple, oral Recommended Dose: 2 mg, 2 times / day Route: oral Route: multiple Dose: 2 mg, 2 times / day Sources: Page: p.4 |
unhealthy, 14–18 n = 21 Health Status: unhealthy Condition: Autism spectrum disorders Age Group: 14–18 Sex: M+F Population Size: 21 Sources: Page: p.4 |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
modest [IC50 348 uM] | ||||
yes [IC50 0.75 uM] | ||||
yes [IC50 7.6 uM] | ||||
yes [IC50 77.5 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes |
PubMed
Title | Date | PubMed |
---|---|---|
External Cl(-)-dependent formation of watery vacuoles by long-term hypotonic shock in 3T3-L1 cells. | 2001 |
|
Solubilization and stability of bumetanide in vehicles for intranasal administration, a pilot study. | 2001 |
|
Effect of chloride channel blockers on anti-IgE-stimulated histamine and IL-4/IL-13 release from human basophils. | 2001 Apr |
|
Differential roles of the sodium-calcium exchanger in renin secretion and renal vascular resistance. | 2001 Aug |
|
Effects of thiazide- and loop-diuretics, alone or in combination, on calcitropic hormones and biochemical bone markers: a randomized controlled study. | 2001 Aug |
|
Loop diuretics and in vitro relaxation of human fetal and newborn mouse airways. | 2001 Aug |
|
"Avian-type" renal medullary tubule organization causes immaturity of urine-concentrating ability in neonates. | 2001 Aug |
|
Protection of ischemic myocardium in diabetics by inhibition of electroneutral Na+-K+-2Cl- cotransporter. | 2001 Aug |
|
Insulin-independent, MAPK-dependent stimulation of NKCC activity in skeletal muscle. | 2001 Aug |
|
Cl(-)-dependent secretory mechanisms in isolated rat bile duct epithelial units. | 2001 Aug |
|
Functional and molecular characterization of the K-Cl cotransporter of Xenopus laevis oocytes. | 2001 Aug |
|
Alterations in airway ion transport in NKCC1-deficient mice. | 2001 Aug |
|
Contractile regulation of the Na(+)-K(+)-2Cl(-) cotransporter in vascular smooth muscle. | 2001 Aug |
|
Optical method for quantifying rates of mucus secretion from single submucosal glands. | 2001 Aug |
|
Contribution of the Na-K-Cl cotransporter on GABA(A) receptor-mediated presynaptic depolarization in excitatory nerve terminals. | 2001 Aug 15 |
|
Cisplatin-induced apoptosis of mesothelioma cells is affected by potassium ion flux modulator amphotericin B and bumetanide. | 2001 Aug 15 |
|
Potentiation of urinary atrial natriuretic peptide interferes with macula densa function. | 2001 Aug 15 |
|
Growth factors stimulate the Na-K-2Cl cotransporter NKCC1 through a novel Cl(-)-dependent mechanism. | 2001 Dec |
|
Liquid and ion transport by fetal airway and lung epithelia of mice deficient in sodium-potassium-2-chloride transporter. | 2001 Jul |
|
Effects of the potassium channel blocker barium on sodium and potassium transport in the rat loop of Henle in vivo. | 2001 Jul |
|
Epinephrine-induced increases in [Ca2+](in) and KCl-coupled fluid absorption in bovine RPE. | 2001 Jul |
|
Forskolin activation of apical Cl- channel and Na+/K+/2Cl- cotransporter via a PTK-dependent pathway in renal epithelium. | 2001 Jul 27 |
|
Na+-K+-Cl- cotransporter in rat focal cerebral ischemia. | 2001 Jun |
|
Two further British families with the 'cryohydrocytosis' form of hereditary stomatocytosis. | 2001 Jun |
|
Determination and characterization of diuretics in human urine by liquid chromatography coupled to pneumatically assisted electrospray ionization mass spectrometry. | 2001 Jun |
|
cAMP-dependent fluid secretion in rat inner medullary collecting ducts. | 2001 Jun |
|
Endogenous and exogenous Na-K-Cl cotransporter expression in a low K-resistant mutant MDCK cell line. | 2001 Jun |
|
Application of multiple response optimization technique to extended release formulations design. | 2001 Jun 15 |
|
K(+) transport in red blood cells from human umbilical cord. | 2001 Jun 6 |
|
Ca++ regulation of paracellular permeability in the middle intestine of the eel, Anguilla anguilla. | 2001 Mar |
|
Pharmacokinetics and pharmacodynamics of intravenous bumetanide in mutant Nagase analbuminemic rats: importance of globulin binding for the pharmacodynamic effects. | 2001 May |
|
HCO3- potentiates the cAMP-dependent secretory response of the human distal colon through a DIDS-sensitive pathway. | 2001 May |
|
Diverging effects of 5-HT3 receptor antagonists ondansetron and granisetron on estramustine-inhibited cellular potassium transport. | 2001 May |
|
Pulmonary oedema after ophthalmic regional anaesthesia in an unfasted patient undergoing elective surgery. | 2001 May |
|
Role of renocortical cyclooxygenase-2 for renal vascular resistance and macula densa control of renin secretion. | 2001 May |
|
Identification and characterization of human organic anion transporter 3 expressing predominantly in the kidney. | 2001 May |
|
Ethanol-induced swelling in neonatal rat primary astrocyte cultures. | 2001 May 11 |
|
Role of Cl- current in endothelin-1-induced contraction in rabbit basilar artery. | 2001 Nov |
|
Vacuolation induced by VacA toxin of Helicobacter pylori requires the intracellular accumulation of membrane permeant bases, Cl(-) and water. | 2001 Nov 23 |
|
Ionic mechanisms of GABA-induced long-term potentiation in the rat superior colliculus. | 2001 Oct |
|
Mechanism(s) of chloride transport in human distal colonic apical membrane vesicles. | 2001 Oct |
|
Mechanism of substance P-induced liquid secretion across bronchial epithelium. | 2001 Sep |
|
Contribution of the Na(+)-K(+)-2Cl(-) cotransporter (NKCC1) to transepithelial transport of H(+), NH(4)(+), K(+), and Na(+) in rat outer medullary collecting duct. | 2002 Apr |
|
Renal Na-K-Cl cotransporter NKCC2 in Dahl salt-sensitive rats. | 2002 Apr |
|
NKCC2: a drug target in hypertension. | 2002 Apr |
|
Steroids modulate transepithelial resistance and Na(+) absorption across cultured porcine vas deferens epithelia. | 2002 Apr |
|
Chloride transport in rabbit esophageal epithelial cells. | 2002 Apr |
|
Interleukin-13 induces a hypersecretory ion transport phenotype in human bronchial epithelial cells. | 2002 Feb |
|
Intrinsic optical signals in the rat optic nerve: role for K(+) uptake via NKCC1 and swelling of astrocytes. | 2002 Feb |
|
Effects of butyrate on active sodium and chloride transport in rat and rabbit distal colon. | 2002 Feb 15 |
Patents
Sample Use Guides
In Vivo Use Guide
Curator's Comment:: Parenteral Administration: The usual initial dose is 0.5 to 1 mg intravenously or intramuscularly. Intravenous administration should be given over a period of 1 to 2 minutes. If the response to an initial dose is deemed insufficient, a second or third dose may be given at intervals of 2 to 3 hours, but should not exceed a daily dosage of 10 mg.
The usual total daily dosage of Bumetanide is 0.5 mg to 2 mg and in most patients is given as a single
dose.
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17681355
10 uM of bumetanide reduced amplitude and frequency of ictal-like events (ILE) induced by 8.5 mM K(+), but it increased the frequency of ILE induced by 1 microM kainate.
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Jun 26 05:10:47 UTC 2021
by
admin
on
Sat Jun 26 05:10:47 UTC 2021
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Record UNII |
1QC8KM52D1
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Record Status |
Validated (UNII)
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Record Version |
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-
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28434-74-4
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249-015-6
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1QC8KM52D1
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23696786
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PARENT -> SALT/SOLVATE |